The Gabriel reagent is widely used as a nucleophilic aminating agent since its reactivity is reliable and its handling is easy. Recently, a variety of aminating agents analogous to the Gabriel reagent have been reported, for example, tert-butyl methyl iminodicarboxylate, N-(tert-butoxycarbonyl)-p-toluenesulfonamide, sodium diformamide, and di-tert-butyl iminodicarboxylate.

The potassium salt of imide 1 reacts with alkyl halide to give imide 2. 2 is treated with base or acid to give either N-Boc-amine 3 or N-metoxycarbonylamine 4, respectively. Moreover, 1 also serves as an acid nucleopile in the Mitsunobu reaction to allow for the conversion of hydroxyl groups to amino groups. Therefore, 1 is a useful reagent to give mono protected amines.
On the other hand, acetoxime O-(2,4,6-trimethylphenyl)sulfonate 5 has been reported as a useful electrophilic aminating agent. 5 reacts with Grignard reagent in the presence of a catalytic amount of magnesium chloride to afford primary amines in good yields.

A1137	A1441	A1341
I0497	B1734	D2361
D1672	M1182	H0093
H0258	H0196	H0530
I0510	D1899	B2303
B1648	A1632	C1757
M0343	M0886	P1235
P0403	D2479	B2857
T1184

A1137	4-Amino-1,2,4-triazole
A1441	Acetoxime O-(2,4,6-Trimethylphenylsulfonate)
A1341	Azidomethyl Phenyl Sulfide
I0497	Di-tert-butyl Iminodicarboxylate
B1734	Diethyl N-(tert-Butoxycarbonyl)phosphoramidate
D2361	Diethyl Phosphoramidate
D1672	Diphenylphosphoryl Azide
M1182	Ethyl O-Mesitylsulfonylacetohydroxamate [Precursor of the Powerful Aminating Reagent]
H0093	Hexamethylenetetramine
H0258	Hydroxylamine Hydrochloride
H0196	Hydroxylamine Sulfate
H0530	Hydroxylamine-O-sulfonic Acid
I0510	Iminodicarboxylic Acid tert-Butyl Methyl Ester
D1899	N,O-Dimethylhydroxylamine Hydrochloride
B2303	N-(tert-Butoxycarbonyl)-2-nitrobenzenesulfonamide
B1648	N-(tert-Butoxycarbonyl)-p-toluenesulfonamide
A1632	N-Allyloxycarbonyl-2-nitrobenzenesulfonamide
C1757	N-Carbobenzoxy-2-nitrobenzenesulfonamide
M0343	O-Methylhydroxylamine Hydrochloride
M0886	O-Methylhydroxylamine Hydrochloride (ca. 40% in Water, ca. 5.4mol/L)
P1235	Phthalimide DBU Salt
P0403	Phthalimide Potassium Salt
D2479	Sodium Diformylamide
B2857	tert-Butyl [Bis(4-methoxyphenyl)phosphinyloxy]carbamate
T1184	Trimethylsilylmethyl Azide